Skill Detail

Diagnose Tailscale and proxy conflicts before remote development stalls out

Use tunnel-doctor in Claude Code when Tailscale partially works but SSH, browser, git, or Docker paths fail because proxy, route, or double-tunneling conflicts need a structured diagnosis.

Runbooks & DiagnosticsClaude Code
Runbooks & Diagnostics Claude Code Security Reviewed
Tool match: claude-code-skills MIT license
INSTALL WITH ANY AGENT
npx skills add agentskillexchange/skills --skill diagnose-tailscale-and-proxy-conflicts-before-remote-development-stalls-out Copy
Works best when you want a reusable capability, not another fragile one-off prompt.
At a glance
Tools required
Read, Grep, Edit, Bash
Install & setup
Install the tunnel-doctor skill from daymade/claude-code-skills into Claude Code, then invoke it when Tailscale and proxy or VPN layers coexist on macOS and remote development paths fail inconsistently.
Author
daymade
Publisher
Github Skill
Last updated
Apr 22, 2026
Quick brief

tunnel-doctor is a Claude Code skill for diagnosing and fixing multi-layer conflicts between Tailscale and proxy/VPN tooling on macOS. It walks an agent through symptom-based checks for route hijacking, HTTP proxy environment variables, system proxy bypass, SSH ProxyCommand double tunneling, and VM or container proxy propagation, including remote development and WSL-over-Tailscale edge cases.

How it works

What this skill actually does

Invoke this instead of using Tailscale, Shadowrocket, Clash, Surge, Docker, or SSH normally when basic connectivity signals are misleading β€” for example when tailscale ping works but SSH times out, curl and browser disagree, git push fails through relays, or Docker image fetches break behind TUN and proxy layers. The scope boundary is clear: this is not a product listing for Tailscale or proxy software. It is a repeatable operator runbook for isolating the failing network layer and applying the right remediation path inside a Claude Code troubleshooting workflow.